You may have noticed that the site hasn't been that busy lately. I will give your question a whirl but really you need to read lots more of what is already on here. I'm not really a coach so I'm going to give you a few links to get you started.
My first thought is about your 2:00 and 4:30 goals. I could start with the idea that a 56 400 is unlikely to support a 2:00 800 but without knowing your 200 time, I could be wrong. Anyway, I think there is a bigger problem with goals that was discussed here: viewtopic.php?f=3&t=2147&hilit=goals+problems
Search fallacy of goals if the link doesn't work
There is also a lot on here about HS athletes who ask for help but don't really have control of their training plan because they have HS coaches. Without knowing more, it looks like you overtrained last fall and winter so you need a plan that you are going to be able to do week after week without blowing up. I would start hereviewtopic.php?f=3&t=894&hilit=three+day+rotation
Search lower mileage but still effective if the link doesn't work
After your season, instead of taking a week or two off, run two weeks of the three day rotations but divide all workouts in HALF. So 2.5 miles per day with say 1 mile in zone 2 on day 2 and 1 mile in zone 3 on day 3. You probably want to put in an extra day in zone 1 so that two cycles plus the extra day in zone 1 covers 1 week so you know you will be doing zone 3 on particular days of the week.
For another two weeks build up to Tom's first week, most likely sticking with the extra day in zone 1. Build up means alternating full (5 mile) and half (2.5 mile) versions of the cycle days Then go through the months of Tom's buildup with the extra zone 1 day. Only once you truly know that you can handle the hardest version of the schedule (6 miles per day, hill charges and 100s) in 7 days should you try to pull out the extra day in zone 1.
Good luck. Remember there are lots of other schedules on here, even if you like this one, you should go read about the others because most of the best ideas are spread far and wide and you just have to dig them out.